Blake Walsh

15 Best Things to Do in Milton, MA

  • Published 2022/10/08

Milton in Norfolk County, Massachusetts, is an affluent town south of Boston with tree-lined avenues, historic landmarks, and large areas of preserved open space.

As of 2020, it has a population of 28,630.

Originally called Uncataquisset after an Algonquin phrase for “head of tidewater,” the area was renamed Milton after Milton Abbey in Dorset, England, after its incorporation in 1662.

Milton saw the rise of notable figures, including US President George H.W. Bush, T.S. Eliot (who attended Milton Academy), and Buckminster Fuller (a renowned architect).

The town frequently serves as a filming location because of its opulent surroundings, and scenes from films such as The Social Network, The Judge, and Man of Steel were filmed here.

Although it is relatively quiet compared to Boston, the town of Milton is rich in culture.

It offers a wide variety of outdoor pursuits.

Read on to discover the best things to do in Milton, Massachusetts!

Spot the Wildlife at Blue Hills Reservation

The waters of Blue Hills Reservation

Ryan McGurl /

Blue Hills Reservation occupies a vast portion of southern Milton and includes the eponymous mountain range.

The 635-foot-tall Great Blue Hill is the highest point in Milton’s 22-peak mountain chain.

The Blue Hills Skyline Trail is a 15-mile rollercoaster that crosses the mountain ridge, providing breathtaking vistas of the Boston metropolitan area and the Harbor Islands.

Trail at Blue Hills Reservation

Ryan McGurl /

You may enjoy hiking, mountain biking, horseback riding, skiing during winter, and wildlife spotting.

Blue Hills Reservation is home to several species at risk of extinction in Massachusetts, including the copperhead snake and timber rattlesnake.

Dogwoods and lady’s slippers grow there, and there are also white-tailed deer, red foxes, coyotes, and turkey vultures.

Discover Milton’s Natural History at the Blue Hills Trailside Museum

Located along Canton Avenue, the Blue Hills Trailside Museum haswelcomedg visitors to its museum since 1959.

Natural history displays and many cages for local animals come together at the museum, making it the leading interpretive site for the Blue Hills Reservation.

It features rescued River Otter and Red Foxes that would otherwise perish in their natural habitats.

These displays are ideal for kids of all ages.

The Blue Hills Trailside Museum hosts various seasonal events, from a primer on birdwatching to an exploration of the science underlying the monarch butterfly’s annual flight from Canada to Mexico.

There is a gift store in the museum where you can purchase works by local artists, engaging playthings for kids, and innovative equipment for outdoor adventures.

Admire the Architecture of the Eustis Estate

Exterior of the Eustis Estate

Suzanne Grudem, CC BY-SA 4.0, via Wikimedia Commons

The Eustis Estate, built at the end of the 19th century, sits on 80 lush acres on Canton Avenue.

The eclectic home on the estate, built by renowned architect William Ralph Emerson and constructed in 1878 for William Ellery Channing Eustis, is a notable example of Late Victorian architecture.

Its original architectural intricacies and design aspects set this stone structure apart from other historic homes in the Boston region.

Historic New England bought the property in 2012.

Since then, visitors have been able to take tours of the grounds protected by a charming gatehouse.

The Eustis Estate includes three galleries that display works from its permanent collection and temporary exhibitions of antiques, photographs, and ephemera.

See Various Tree Species at Mary M.B. Wakefield Arboretum

The Davenport family owned an estate on the west side of Brush Hill Road for more than 3oo years before donating it to a nonprofit organization in 2004.

The Mary May Binney Wakefield was the final inhabitant of the Wakefield Estate.

She acquired it in 1952 and was a well-known gardener and landscape architect involved in several local gardening groups.

Located on Brush Hill Road, the Mary M.B. Wakefield Arboretum is open for tours on its 22 acres.

The landscape, which Wakefield cultivated, includes formal gardens, woods, orchards, and marshes.

Over 300 kousa dogwood trees reach full bloom every June, marking the year’s pinnacle at Dogwood Days.

Step Back into the Past at the Forbes House Museum

Exterior of the Forbes House Museum

Jameslwoodward, CC BY-SA 3.0, via Wikimedia Commons

Located on Adams Street, the Forbes House Museum offers sweeping views of the city and its neighboring areas.

It lies atop the Neponset tribe’s ancestral land.

In the latter part of the 1700s, the state’s final royal governor, Thomas Hutchinson, set his house here.

This Greek Revival style home included indoor plumbing and central heating, which were revolutionary at the time.

Until 1962, the residence housed members of the Forbes family for four generations.

The Forbes House Museum showcases their international travels, business successes, and charitable contributions.

The collection includes artifacts, exported porcelain, Chinese furniture, and works of art.

You may also find Victorian-era novelties and accessories, artifacts from Captain Forbes’s 1847 Ireland mission, and Civil War and Lincoln memorabilia.

The museum first appeared on the National Register of Historic Places (NRHP) in 1966.

Catch a Hockey Game at Ulin Memorial Rink

In Milton, there is a public ice rink called Ulin Memorial Rink.

There is a sign in the foyer proclaiming the rink to be the first public skating rink in the United States, and its construction date of 1953 lends credence to this claim.

It was initially open-air but became enclosed in 1978.

Improvements were made again in 1998 and again in 2010.

The Department of Conservation used to own and manage the ice rink.

However, on behalf of the city of Milton, Curry College has operated the building since 2010.

The Milton High School hockey team and the Commonwealth Figure Skating Club call this facility home.

Spend the day on the ice, skating, or watching a hockey game at Ulin Memorial Rink.

Admire the Panoramic Views from Eliot Tower

Exterior of the Eliot Tower

Adam Gladstone /

Eliot Tower in Blue Hills Reservation offers 270-degree views of the Blue Hills and the Boston cityscape.

It became part of the National Register of Historic Places in 1980.

After a strenuous uphill slog, sightseers may enter the tower’s stone walls and ascend stairs to the observation deck at the very top.

Daytime view of the Eliot Tower

Jameslwoodward, CC BY-SA 3.0, via Wikimedia Commons

Magnificent scenery is the payoff for your efforts.

You can’t go wrong with a visit to Eliot Tower each season of the year.

Stroll around Cunningham Park

Mary A. Cunningham established a trust to aid the residents of Milton after her death in 1904.

The trustees bought the 100+ acre land and opened Cunningham Park to the public in 1905.

Still owned and administered by a private foundation, Cunningham Park is centered on a large swimming area, The Pond, which is nearly an acre in size.

The park on Edge Hill Road is home to Victory Gardens, a collection of open fields, woodland paths, and concrete walkways.

It also features a large swimming pond, a brand-new playground, and a multi-purpose event center with bowling alleys.

Cap off Your Day with a Drink at Steel & Rye

Steel & Rye, run out of a garage on Eliot Street, derives its inspiration from the area’s rich heritage.

The site served as a farming, milling, and manufacturing hub due to its location on the city’s outskirts.

Steel & Rye is proud to celebrate such a rich American history.

In 2012, Dan Kerrigan and Bill Scannell opened Steel & Rye as co-owners.

Classic Americana inspires everything from the menu to the atmosphere.

Its beverage section reflects its food philosophy.

It offers craft beers, cocktails with an American twist, and boutique wines from the United States and worldwide.

In a constantly changing display, you get to try numerous unique items.

The food on the menu is to die for, too.

Steel & Rye’s menu is built on handcrafted ingredients and traditional techniques by chefs who will spark your imagination.

It boasts using only farm-raised beef and poultry, wild-caught fish, and heirloom and heritage grains.

Go Swimming at Houghton’s Pond

The waters of Houghton's Pond

kforce214 /

You may visit the Blue Hills Reservation during the warmer months to enjoy Houghton’s Pond.

It is a kettle hole pond, a type of pond supplied by a spring formed when glaciers retreated in the last ice age.

Located on the northern side of Houghton’s Pond, the beach features a roped-off swimming area, changing rooms, and picnic tables.

Trees near Houghton's Pond

Nature’s Charm /

Lifeguards are often on duty from Memorial Day weekend until Labor Day.

You may park here and walk to the paths that wind through the forested hills to the east, and there’s also a playground and several sports facilities nearby.

Stick to the paths for hiking, bicycling, or horseback riding.

Aerial view of Houghton's Pond

Adam Gladstone /

Conquer the High Ropes Course at New England Base Camp

In search of a weekend adventure?

Check out New England Base Camp on Unquity Road.

Visitors of all ages can use the facility’s many amenities, including a high ropes course, rock climbing/bouldering areas, an archery range, and more.

In addition, scouts of all ranks can participate in activities at New England Base Camp.

Meanwhile, its instructional offerings complement the Common Core State Standards and the Massachusetts Curriculum Frameworks for field excursions.

For a day of stimulating education, it offers STEM activities, high ropes courses, and cooperative programs for students who learn at home.

In addition, the venue hosts business outings and team-building exercises.

There are various places to stay the night, including cabins, Adirondack shelters, and campsites.

Join the Art Classes at the Milton Art Center

Located on Edge Hill Road, the Milton Art Center is a nonprofit organization that hosts art-related classes and exhibitions for people of all ages.

Clay, oil painting, and sketching are just a few mediums in its youth and adult art classes.

In 2012, it opened at its current location in East Milton Square, Milton.

In addition to providing art instruction, the group also uses its gallery as a gathering place to feature the works of local artists, craftspeople, singers, comedians, and authors.

Additionally, it hosts art-themed birthday parties and offers all of the necessary supplies.

Profits from events and charitable contributions support the Milton Art Center.

Have a Picnic at Governor Hutchinson’s Field

The grounds of Governor Hutchinson's Field

Jameslwoodward, CC BY-SA 3.0, via Wikimedia Commons

Governor Hutchinson’s Field is a 10-acre area that slopes down from Milton Hill to the Neponset River.

Thomas Hutchinson, the 12th governor of the Province of Massachusetts Bay, made this a part of his country home in 1734.

Sir Francis Bernard designed the house and garden at Hutchinson’s request.

Indulge yourself in the views of the Boston Harbor Islands, the Boston skyline, and the extensive salt marshes along the Neponset River from Governor Hutchinson’s Field.

Rolling down the hill or having a picnic in the woods after exploring the pathways through the fields is a terrific way to spend a day.

Rejuvenate Yourself at A New You Spa

Lily Pham opened A New You Spa in Milton in 2012, focusing on health and beauty.

She hopes to maintain the highest standards in her field, and she does it by regularly studying for and taking new certification exams.

Furthermore, she stresses the need for employees’ ongoing professional development.

Before transitioning to health, she got her feet wet in the manicure and skincare industry.

Visit this spa on Central Avenue, for a one-of-a-kind experience and a specialized face treatment.

Elevate the look of your nails with expert nail techs.

After getting your hair done at this spa, you’ll feel like a stunning bombshell.

Spagoers may get customized massages from trained professionals here.

Having such a wide variety of services available, A New You Spa is a great place to spend time and relax.

See the Historic Structures at Milton Centre Historic District

A church at Milton Centre Historic District

John Phelan, CC BY-SA 3.0, via Wikimedia Commons

Milton Centre Historic District lies on Canton Avenue, west of Reedsdale Road.

In 1727, Milton constructed its third meetinghouse on Academy Hill.

It was replaced by the First Parish Church in 1788, making it the oldest structure in the Milton Centre Historic District.

On these 11 acres, you’ll find 11 historic structures, including the unassuming-looking Powder House, constructed in 1811 in anticipation of war with the British.

Also of note are the Milton Public Library (1902), built in the Beaux-Arts style, and the Chemical Engine House (1881).

The Lira Bandstand, located in front of the town hall, hosts several performances during the summer.

Final Thoughts

Treat yourself and your loved ones to the best things to do in Milton, Massachusetts.

Explore on foot to have a more profound familiarity with the neighborhood.

Whether you’re an outdoor junkie or a history buff, this place has something for you.

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